Nitya G. Kundu

Studies on copper(I) catalysed cross-coupling reactions : A convenient and facile method for the synthesis of diversely substituted α,β-acetylenic ketones☆

Abstract Terminal alkynes reacted with acid chlorides in the presence of cuprous iodide as a catalyst in Et 3 N at room temperature yielding a number of α,β-acetylenic ketones in good to excellent yields.

Palladium-catalyzed heteroannulation with acetylenic carbinols as synthons-synthesis of quinolines and 2,3-dihydro-4(1H)-quinolones

Abstract o -Iodoanilides 4 reacted with terminal acetylenic carbinols 5 under palladium-catalyzed conditions to yield o -substituted anilides 6 . Most of the anilides 6 could be cyclized with NaOEt/EtOH to 2-arylquinolines 2 . o -Iodoanilines 7 reacted with carbinols 5 leading to 8 which on palladium(II) assisted cyclisation afforded substituted quinolines 2 . An excellent synthesis of the alkaloid dubamine (2n) is reported. Also, the anilides 6 on acid-catalyzed rearrangement, deprotection and cyclisation led to the 2-aryl-2, 3-dihydro-4(1H)-quinolones 16 .

Heteroannulation through combined palladium catalysed and Friedel-Crafts reactions strategy: Synthesis of 3-alkylidene isoindolin-1-ones☆

Abstract The palladium-catalysed reactions of 2-iodobenzamides 1–5 with trimethylsilyl acetylene 6 led to 2-(2-trimethylsilyl)ethynyl benzamides 7–11 in excellent yields. The 2-(2-trimethylsilyl)ethynyl benzamides 7–11 underwent Friedel-Crafts reactions with acid chlorides 12–17 or anhydride 18 smoothly under mild conditions yielding the 3-alkylidene isoindolin-1-ones 19–38 .

Synthesis of quinolines and 2,3-dihydro-4(1h)-quinolones. Palladium catalysed reaction of o-iodoanilides with acetylenic carbinols

Abstract A facile and general synthesis of quinolines and 2,3-dihydro-4(1H)-quinolones was accomplished, through palladium catalysed reaction of o-iodoanilides with acetylenic carbinols.

An Efficient Method for the Iodination of C5-Position of Dialkoxy Pyrimidines and Uracil Bases1,2

Abstract N-Iodosuccinimide in trifluoroacetic acid and trifluoroacetic anhydride was found to be an excellent reagent for the conversion of 2,4-dialkoxy pyrimidines to 2,4-dialkoxy-5-iodopyrimidines. Iodination at C5-position of uracil and its derivatives was also accomplished with the above reagent.

Copper(I)-catalysed acylation of terminal alkynes

Abstract A facile synthesis of conjugated acetylenic ketones is reported, involving Copper(I) catalysed acylation of terminal alkynes with acyl halides.

Synthesis and biological activities of [E]-5-(2-acylvinyl)uracils

Abstract The synthesis of a number of 5-substituted uracils, eg [ E ]-5-(2-acylvinyl)uracils 8a–8g is described. These compounds were found to have cytotoxic activities against CCRF-CEM human lymphoblastoid cells, HT-29 colon carcinoma cells and L1210/0 mouse leukemia cells. These compounds were also found to inhibit thymidylate synthase.

A convenient and highly regio and stereoselective method for the synthesis of (E)-3-alkylidene isobenzofuran-1(3H)-ones (phthalides)

Abstract 2-Iodobenzyl alcohol on treatment with acetylenic carbinols in the presence of a palladium catalyst and copper(I) iodide as a co-catalyst afforded disubstituted alkynes. Jones oxidation of the disubstituted alkynes led to (E)-3-alkylidene isobenzofuran-1(3H)-ones in good yields in a highly regio and stereoselective manner. The E-isomers were obtained exclusively instead of the more stable Z-isomers.

An unusual cleavage of a C–S bond with concurrent S-arylation under palladium–copper catalysis

3-[2-(N-p-Toluenesulfonyl)aminophenylthio]prop-1-yne (4) reacted with aryl iodides 5–14 under palladium–copper catalysis to afford (2-arylthio)-p-toluenesulfonanilide (15–23) in moderate to good yields (54–64%) through unusual depropargylation and S-arylation reactions.

Palladium-catalyzed synthesis of [E]-6-(2-acylvinyl)uracils and [E]-6-(2-acylvinyl)-1-[(2-hydroxyethoxy)methyl]uracils—their antiviral and cytotoxic activities☆

[E]-6-(2-Acylvinyl)uracils and their corresponding 1-(2-hydroxyethoxy)methyl derivatives were synthesized through palladium-catalyzed reactions which involved an interesting rearrangement. Some of the acylvinyl uracils (3, 4, and 5) and the acyclonucleosides (8 and 10) showed pronounced activity against human T-lymphocyte Molt 4/C8 and CEM cells. However, they were less toxic to murine L1210 and FM3A cells. The compounds did not have any marked antiviral activity.